Reese Witherspoon's Major Post-Divorce Transformations

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Reese Witherspoon isn't just one of Hollywood's most beloved and influential stars. Though famous for iconic roles like Elle Woods in the "Legally Blonde" franchise, Madeline Mackenzie in "Big Little Lies," and Bradley Jackson in "The Morning Show," the bubbly and ambitious actor has also made waves as a producer, a savvy entrepreneur, an author, and a fervent champion of gender equality in the entertainment industry.

That's a lot to juggle, but, fortunately, she has also relied on the support and love of her celebrity friends and significant others over the years, including two ex-husbands: Ryan Phillippe (1999-2008) and Jim Toth (2011-2023). While her divorce from the latter was rather seamless, her split from the former was much more dramatic and publicized and left her feeling emotionally exhausted. Even her career suffered for a few years. Still, she picked up the pieces and reinvented herself after each separation, revenge dresses on the red carpet included.

Currently, she's focused on a variety of projects as well as her physical and mental wellbeing and her children, Ava Phillippe, Deacon Phillippe, and Tennessee Toth. She has also built herself a media empire (most of which she sold in 2021), which has catapulted her net worth to $440 million, as reported by Forbes.

So, let's revisit some of Witherspoon's most important milestones and challenges following each split.

Reese Witherspoon and Ryan Phillippe met at her 21^st birthday party and reconnected on the set of "Cruel Intentions" in 1998. They exchanged vows in South Carolina on June 5, 1999, when she was six months pregnant with Ava. Sadly, though their relationship was a passionate one, the couple officially split in October 2006, citing irreconcilable differences amid rumors of Phillippe's affair with Australian actor Abbie Cornish. "That was a tough year that followed," Witherspoon admitted on "60 Minutes" in 2014 (via UPI). "I spent a few years just trying to feel better. You can't really be very creative when you feel like your brain is scrambled eggs."

To make matters worse, she was raising her children in Los Angeles at the time, and the paparazzi wouldn't leave them alone. "I remember at church once in L.A., a guy jumping on the hood of the car and on each side, three people pushing against the window banging on the door when my kids were little after I got a divorce and chasing us like it was a police chase, down the freeways," she recalled in an interview with The New York Times in 2025. "It was terrifying. It was really hard on my kids. Anxiety-producing. I really regret living in L.A. during that time."

Thankfully, she found all the support she needed in therapy and in her small circle of women friends, which included Jennifer Garner.

Following a painful breakup, many people, celebrities included, transform their appearance and image as a symbol of a fresh start. The changes in Reese Witherspoon were noticeable in 2007, when she started adopting a healthier lifestyle that involved yoga, exercising, and a balanced diet — under the guidance of celebrity fitness trainer Michael George.

Subsequently, at the 2007 Golden Globes (her first red carpet appearance since her split from Ryan Phillippe), the actor debuted a sharp layered haircut with side bangs. She also opted for a bolder makeup look than usual and confidently showed off her toned figure in a knee-length, bright yellow Nina Ricci bustier cocktail dress. The press labeled the latter a "revenge dress," especially because she cheekily paired it with red sandals.

Then, in 2008, at the "Four Christmases" premiere, Witherspoon showed up at Grauman's Chinese Theater in another Nina Ricci bustier dress, sporting a gold collar necklace and a glamorous side-parted Hollywood Golden Age do. The boho girl next door her fans and the media had been so used to was truly nowhere to be seen.

In between her two marriages, Reese dated another high-profile actor for two years: Jake Gyllenhaal, who was five years her junior. Even though they had met before, they hit it off immediately after reconnecting on the set of "Rendition" in Morocco in 2006. He was exactly what she needed to blow off some steam, and even if she denied being romantically involved with him at first, she did publicly gush over him on multiple occasions. "He is just wonderful," she told Ellen DeGeneres in 2007 (Via Us Weekly). "He's very kind, generous and funny. Yeah, he's great, and I look forward to maybe making another film with him."

Still, the pair called it quits around Thanksgiving 2009. Apparently, it was Witherspoon who initiated the split because Gyllenhaal was pressuring her to get married, and she certainly wasn't ready for that type of commitment again.

Reese Witherspoon may have turned down a marriage proposal from Jake Gyllenhaal, yet she accepted one from talent agent Jim Toth within less than a year of dating. The pair met through a mutual friend and were first spotted together having dinner in Santa Monica in February 2010. By the end of the year, they were officially engaged.

In a 2012 interview with Elle, the "You're Cordially Invited" star shared her deep appreciation for Toth's positive influence in her life, recalling, "Jim said, 'I'm gonna show you every day what a good partner is, what a good person is. I'm going to take care of you. I'm gonna do this so much that you're gonna get used to it.' I was, like, 'What are you talking about?' I've never had anybody like that in my life." Indeed, that statement marked the moment she chose to shed the emotional baggage of her past relationships and move on with a more suitable partner.

The blissful couple exchanged their vows at Witherspoon's California ranch in March 2011 and welcomed a baby boy, Tennessee James, in September 2012.

Following her first divorce, Reese Witherspoon went through a dry spell professionally; her movies, including "Four Christmases" and "How Do You Know," weren't performing very well, and she wasn't feeling creative. As she told "60 Minutes" in 2014 (via UPI), "I was just kind of floundering career-wise cause I wasn't making things I was passionate about, I was just kinda working. It was really clear the audiences weren't responding to anything I was putting out there."

So, in 2012, she cemented her professional future when she co-founded the production company Pacific Standard (which would later become part of her media group, Hello Sunshine), focusing on developing strong female lead characters. As such, in 2014, she produced the highly acclaimed "Gone Girl" and produced and starred in the hit R-rated biopic "Wild." The latter even earned her a Best Actress Oscar nomination. It was based on a memoir by Cheryl Strayed, who backpacked the Pacific Coast Trail in 1995, and Witherspoon insisted on being as faithful to the book as possible. Though working on this film completely drained her emotionally, it marked a positive shift in her acting roles. "Without any hyperbole, it's the hardest thing I've ever had to do in my entire working life," she admitted to Time Out in 2015.

In addition to her film roles, Reese Witherspoon has appeared in and voiced various television movies and series, including playing the spoiled and materialistic Jill, Rachel Greene's (Jennifer Aniston) younger sister, on "Friends."

More recently, she garnered widespread acclaim as the righteous, overprotective, and witty Madeline Mackenzie in the HBO dark comedy series "Big Little Lies," opposite Nicole Kidman, Shailene Woodley, Zoë Kravitz, and Alexander Skarsgård. Witherspoon won a Primetime Emmy Award for producing this show and was nominated for Outstanding Lead Actress in a Limited Series. That particular project meant a lot to her as a fervent feminist, prompting her to tell Vogue in 2017, "It was really fun, it went by really easily ... I've never gotten to work with actresses of this caliber, because we're usually cordoned off and we're the only women in movies. Usually, you're with a group of men and you're the only girl."

Additionally, for the role of Bradley Jackson on the Apple TV+ satire series "The Morning Show," Witherspoon was nominated for a Primetime Emmy Award for Outstanding Lead Actress in 2022 and 2024. This ongoing show has reunited her with Aniston, who spoke very highly of her to Harper's Bazaar in 2023 and declared, "She is one of the most highly productive human beings I've ever encountered. It's incredible."

Though they officially called it quits via Instagram on March 24, 2023, Reese Witherspoon and Jim Toth had actually started dividing their assets two years prior, aiming for a drama-free divorce. They announced their separation shortly after the actress celebrated her 47^th birthday and concluded their statement with (via Us Weekly), "We have enjoyed so many wonderful years together and are moving forward with deep love, kindness, and mutual respect for everything we have created together."

Indeed, their split was amicable and handled with maturity, and the actor chose to prioritize smooth co-parenting and her personal well-being instead. She spent a lot of time unwinding and reflecting on her own. As she told Harper's Bazaar in July 2023, she enjoyed painting and listening to binaural beats for relaxation. "It's better than any melatonin or sleep aid," she said.

To usher in a fresh start in the spring of 2023, Reese Witherspoon spruced up her long, layered hair with fresh, youthful fringe bangs, which she debuted on Instagram on May 23, 2023. "I love the South," she wrote under the garden selfie, which captured her radiant smile and highlighted her glowing complexion under minimal makeup.

The born-and-bred Southerner certainly turned heads when she donned a crimson strapless Elie Saab gown at the 2024 Screen Actors Guild Awards. "It's giving Pookie [referring to TikTok star Campbell Hunt Puckett] looks fire. It's giving ... lady in red," she joked to E!'s Laverne Cox at the time.

The actor has also been relying on a specific fitness regimen that includes running, pickleball, yoga, bicep curls, and Khumbhaka breath retention. It has been vital for preserving her mental and physical wellness.

In 2017, Reese Witherspoon launched the "Reese's Book Club" Instagram page in order to showcase her favorite feminist titles on a monthly basis. Some recent notable picks include Rebecca Armitage's "The Heir Apparent" and Elliana Ramage's "To the Moon and Back." At the time of publishing, the account has garnered 3.1 million followers. There's also a website, reesesbookclub.com, that features a blog.

"Where the Crawdads Sing," by Delia Owens, was also featured, and, in 2022, it was adapted into a film by Hello Sunshine, the production company Witherspoon still co-owns. "Every artisan on this movie worked so hard to make that book come to life ... To have this story of this young woman who's just surviving on her own in the wilderness was so beautiful, and I was just really moved by that," the actor gushed in an interview for Reese's Book Club.

This endeavor isn't Witherspoon's sole contribution to the literary world, though. She also co-authored the female-led thriller "Gone Before Goodbye" with Harlan Coben, which hit shelves on October 14, 2025. This work highlighted her eagerness to introduce a female action hero similar to James Bond or Jason Bourne — her own answer to "the girl in the bikini or the girl stirring her drink," as she sarcastically told CBS News at the time.

So, what's next for the multitalented, business-savvy, and ever-optimistic Reese Witherspoon? As far as her romantic life is concerned, she's been seeing German financier and New York Islanders' co-owner Oliver Haarmann since 2024. A source told People in October 2024, "Reese is doing great and enjoys dating. She's having fun with Oliver. She often flies between Nashville and NYC to see him. He's spending time with her kids too." The pair were also spotted hugging and kissing in Saint-Tropez, France, in July 2025.

Career-wise, Witherspoon is balancing many projects simultaneously, including executive-producing the "Legally Blonde" prequel series, "Elle," which will likely debut on Prime Video in the summer of 2026. "I truly couldn't be more excited about this series!" she said in a statement. "Fans will get to know how Elle Woods navigated her world as a teenager with her distinct personality and ingenuity, in ways that only our beloved Elle could do. What could be better than that?!"

The actor is also expected to return to "Big Little Lies" for a third season.